Synthesis of (S)-(-)- and (R)-(+)-O-methylbharatamine using a diastereoselective Pomeranz-Fritsch-Bobbitt methodology
Authors:
- Maria Chrzanowska,
- Agnieszka Dreas,
- Maria D. Rozwadowska
Abstract
Laterally lithiated (S)-(-)- and (R)-(+)-o-toluamides 6 with a chiral auxiliary derived from (S)- and (R)-phenylalaninol, respectively, were used as the building blocks and chirality inductors in the asymmetric modification of the Pomeranz-Fritsch-Bobbitt synthesis of isoquinoline alkaloids. Their addition to imine 2 proceeded with partial cyclization, giving isoquinolones (+)-7 and (-)-7 along with acyclic products, (-)-8 and (+)-8, respectively. LAH-reduction of (+)-7 and (-)-7, followed by cyclization, afforded both enantiomers of the alkaloid, (S)-(-)- and (R)-(+)-O-methylbharatamine 5, in 32% and 40% overall yield and with 88% and 73% ees, respectively. © 2005 Elsevier Ltd. All rights reserved.
- Record ID
- UAMb6aedf47157d4b6c80229cccbefb9099
- Author
- Journal series
- Tetrahedron-Asymmetry, ISSN 0957-4166
- Issue year
- 2005
- Vol
- 16
- Pages
- 2954-2958
- ASJC Classification
- ; ; ;
- DOI
- DOI:10.1016/j.tetasy.2005.07.025 Opening in a new tab
- Language
- (en) English
- Score (nominal)
- 0
- Score source
- journalList
- Publication indicators
- = 18; = 17; : 2005 = 0.906; : 2006 (2 years) = 2.468 - 2007 (5 years) =2.460
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- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAMb6aedf47157d4b6c80229cccbefb9099/
- URN
urn:amu-prod:UAMb6aedf47157d4b6c80229cccbefb9099
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.